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Puerto Rico Cruises Starting In October 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2026, 2027 or 2028, we have 28 unique cruise itineraries and 126 departures available, operated by seven of the world's leading cruise lines departing in October.
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28 Cruises (126 Departures)
28 Cruises (126 Departures)
Departures
Duration
8 Days
20 Days
Countries Visited
Start & End Cities
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Operators
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Price
$700pp
$28,620pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Drinks On Us
Inside
$1,692
Oceanview
$1,692
Balcony
$1,951
Suite
$6,571
From (Per Person)
A$1,692
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,561
Oceanview
$1,888
Balcony
$2,175
Suite
-
From (Per Person)
A$1,561
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$1,185
Balcony
$1,442
Suite
-
From (Per Person)
A$1,185
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$784
Oceanview
$962
Balcony
$1,259
Suite
$2,309
From (Per Person)
A$784
Save 16
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$833
Oceanview
$1,041
Balcony
$1,124
Suite
$1,734
From (Per Person)
A$833
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$997
Oceanview
$1,195
Balcony
$1,412
Suite
$6,669
From (Per Person)
A$997
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Allure of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,156
Oceanview
$1,438
Balcony
$1,473
Suite
$8,173
From (Per Person)
A$1,637
Save 183
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,555
Oceanview
$1,609
Balcony
$1,746
Suite
$3,961
From (Per Person)
A$1,885
Save 704
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Operator: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,901
Suite
-
From (Per Person)
A$4,154
Save 282
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departures: Oct 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,663
Oceanview
$1,997
Balcony
$2,135
Suite
$4,472
From (Per Person)
A$1,722
Save 691
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departure: 16 October 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$2,246
Oceanview
$2,909
Balcony
$4,512
Suite
$8,324
From (Per Person)
A$3,224
Save 199
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Caribbean Princess
Departure: 04 October 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$863
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$863
Per Person
View Trip
10 Day New York to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 26 October 2026
Visits: USA, Bermuda, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$4,995
Balcony
$5,872
Suite
$6,262
From (Per Person)
A$4,995
Save 1,605
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Icon Of The Seas
Departure: 10 October 2026
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,692
Oceanview
-
Balcony
$3,595
Suite
$4,337
From (Per Person)
A$2,407
Save 191
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,408
Oceanview
-
Balcony
$1,616
Suite
$1,962
From (Per Person)
A$1,408
Per Person
View Trip
20 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

20 Days (19 Nights) Genoa to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$2,087
Oceanview
$2,444
Balcony
$2,830
Suite
-
From (Per Person)
A$2,087
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$2,126
Balcony
$2,591
Suite
-
From (Per Person)
A$2,126
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$2,067
Balcony
$2,790
Suite
$10,658
From (Per Person)
A$2,067
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 17 October 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,095
Oceanview
$2,216
Balcony
-
Suite
$1,962
From (Per Person)
A$1,566
Save 184
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (6)

10 Days (9 Nights) New York to San Juan
Operator: Azamara
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,666
Oceanview
$3,085
Balcony
$3,783
Suite
$6,474
From (Per Person)
A$2,666
Save 173
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,681
Suite
$10,156
From (Per Person)
A$2,681
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,562
Oceanview
$2,869
Balcony
$3,413
Suite
$5,779
From (Per Person)
A$2,562
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,032
Oceanview
$1,108
Balcony
$1,689
Suite
$2,332
From (Per Person)
A$1,232
Save 857
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Drinks On Us
Inside
-
Oceanview
$1,585
Balcony
$1,786
Suite
$4,578
From (Per Person)
A$1,585
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 23 October 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,796
Oceanview
$1,947
Balcony
$2,027
Suite
$4,176
From (Per Person)
A$2,182
Save 577
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,061
Oceanview
$1,141
Balcony
$1,190
Suite
$1,715
From (Per Person)
A$1,061
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,521
Oceanview
$1,593
Balcony
$1,832
Suite
$5,724
From (Per Person)
A$2,443
Save 40
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,177
Oceanview
$1,261
Balcony
$2,309
Suite
$3,053
From (Per Person)
A$1,415
Save 452
Per Person
View Trip
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